One of the most controversial figures in Long Island history is Richard (Bull) Smith (Smythe), the founder of Smithtown. The owner of lands of vast extent, he was often engaged in boundary disputes. His contest with the town of Huntington over the boundary between it and his own lands was long and bitter, the courts finally deciding in his favor. Richard Smith, Jr., came with his father, Richard Smith, Sr. in 1630, from Gloucestershire, England, to Boston where he married. The young man settled with his father at Taunton, Massachusetts, in 1641; he then purchased a large tract of land on Narragansett Bay and built a trading post at Wickford, Rhode Island. After having trouble with his neighbors in Rhode Island, young Smith removed to the colony of Southampton on Long Island where he again got into difficulty, finally moving to Setauket where he built a home and became a magistrate and public spirited citizen. His wealth permitted him to buy land freely and he soon had assembled a princely domain. He became one of the great men of Colonial Long Island. Smith was buried near his home at Nissequogue.
     The often repeated story about Smith, and one which apparently lacks historical foundation, recounts how he made an
agreement with the Indians that he could have all of the land which he could encircle in one day riding on the back of a bull.  From daylight to dusk he rode, so the legend goes, defining a huge domain. This story, whether true or not, left its mark upon the neighborhood; "Bread and Cheese Hollow" was so named, it is said, because Mr. Smith tarried there on the momentous ride for his noon-day meal.
    The bronze statue of a bull, which was erected on a prominent corner of the village of Smithtown to commemorate Smith's
reputed exploit, has met with considerable disapproval throughout the years on the part of aesthetic- minded citizens. The principal part of Smithtown originally was owned by Lion Gardiner who received it from Grand Sachem Wyandanch in return for a noble service performed by the Englishman. Gardiner procured the ransom of the chief's lovely daughter, Heather Flower, who had been captured on her wedding night by a raiding band of Narragansett Indians and carried off captive to Connecticut.
     In a deed dated July 14, 1659, and witnessed by Richard Smith, Wyandanch in the last year of his life transferred the
Smithtown lands to Gardiner, his friend and benefactor. This deed is in the possession of the Long Island Historical Society in Brooklyn. Before his death in 1663, Gardiner in turn transferred his entire rights to this land to Smith who later obtained a patent on March 3, 1665, from Governor Nicoll of New York.
     The first deed of land from the Indians is dated 1650. Smith was a shrewd businessman and had his deeds recorded with the local authorities on March 2, 1666, and at the same time with the Secretary of State. In subsequent litigation over the boundaries between Smithtown and Huntington, Smith's claims were sustained in the courts.